The feedback is only useful when the person giving it has nothing to lose by being honest.
A buddy back home got into an argument with his boss last week. Called me to vent about it. I was jealous.
Not of the argument. Of having someone in his life who could look at him and say you're wrong about this and it actually meant something. Someone with enough proximity and authority to push back.
I haven't had that in years.
I designed it that way. No boss. No business partner. No employees. No clients who have any real power over me. Three product streams that run whether I show up or not. Total autonomy. The whole point was that nobody could tell me what to do.
Turns out nobody telling you what to do also means nobody telling you when you're full of shit.
That's the trap. You remove every source of friction from your life and then discover the friction was doing something you didn't notice. It was keeping your worst instincts in check. Filing down your dumbest ideas before they cost you money. Making you better even when it pissed you off.
Last month I spent three weeks building out a fourth product stream. Designed it, wrote the copy, set up the whole backend. I was convinced it was brilliant. Then I mentioned it to a woman I'd been talking to over dinner and she asked one question. Who is this for. I didn't have an answer. Three weeks. Not one person in my life had been close enough to the work to ask that before I'd already built the damn thing.
When I ran my logistics company I had a warehouse manager who'd been there longer than me. Knew the operation better than I did in a lot of ways. At least once a month he'd walk into my office and tell me my plan was stupid. Not in those words exactly. But close enough. I'd get annoyed. Then I'd think about it. Then I'd change the plan. Because he was usually right.
I fired him in my head every single week. And he probably saved me from myself a hundred times.
I don't have that person anymore. I have friends who think what I do is cool. Family who don't understand it well enough to question it. An audience that only sees the version I choose to show them. And my own judgment, which is the least reliable voice in the room.
You know this if you've been solo long enough. Maybe you launched something and nobody around you knew enough to say this isn't ready. Maybe you raised your prices and the only feedback came from people who'd never sold anything. Maybe you spent months on a direction that felt right in your own head and wrong everywhere else, but everywhere else didn't have a seat at the table because you'd removed all the chairs.
The dangerous part is it feels like confidence. You make a decision, nobody pushes back, you move forward. Looks like clarity from the outside. But it's not agreement. It's just the absence of anyone who cares enough to disagree.
I don't have a clean answer for this. What I've started doing is small and honestly kind of embarrassing. I send my ideas to three people before I build anything. Not for validation. For resistance. One is my oldest brother who doesn't know a thing about digital products but has a perfect radar for when I'm bullshitting myself. One is a woman I met at a hostel in Porto who runs a small design studio and has zero problem telling me something is bad. And one is a guy I surf with who just asks questions that sit in my chest for days after.
None of them work for me. None of them owe me anything. That's what makes it work. The feedback is only useful when the person giving it has nothing to lose by being honest.
My parents had nine kids and two jobs each and not one second of autonomy their entire lives. Every decision they made ran through somebody else's needs first. It was exhausting. I watched it up close. But they were never confused about whether their choices made sense because the consequences showed up at the dinner table that same night.
I built a life where the consequences take months to arrive. Sometimes longer. And by the time they show up the damage is already done and I'm onto the next brilliant idea nobody bothered to stop me from chasing.
Freedom is the absence of a boss. It's also the absence of the person who would've saved you from yourself.
— Best, Jose
